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Shit tests on a date

Hello guys! I have a few questions to you.

1) Tell me something. I hear this phrase all the time when I sit with a girl on a date. I guess it’s an indicator that girl got bored with me, right? What should I answer in this situation? Should I immediately start to tell her some stories that I know? But in this case won’t it look like I’m some kind of clown that entertains her on her first demand? For some reason it sounds to me as a shit test too, not only as an indicator of boringness.

2) Do you often meet people like that? What do I tell her if she asks do I often approach women on the street, malls or public transportation? Is it a shit test?

3) Where are we going?(on the first date) Should I answer directly: “to the coffee shop” or should I go with intrigue?

4) We don’t know each other that well(when you try to kiss her, touch her or invite her to your place after the club) Maybe there is some kind of routine or metaphor for this one? Some story that I could tell that will make her feel or at least think that it’s not necessary to know someone for ages, that you can get all the important information about the other person in few minutes of meeting. I need this, especially for the clubs. SOS!